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Cheap flights from Canada to Chicago from C$ 149

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
1 Jul — 8 Jul1
1 adult

Cheap flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 26 June 2025.

Round-trip from

C$ 220

One-way from

C$ 149

Popular in

December

Cheapest in

April

Average price

C$ 347

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 155 or less
Porter Airlines
  • Porter Airlines
  • 7/8-10/8
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/7
  • Nonstop
  • 1h 50m total
  • Canada to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 41 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Canada to Chicago (CHI).
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Price to beat on a one-way flight from Canada to Chicago (CHI).
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Find flight deals from Canada to Chicago

Cheapest flights from Canada to Chicago
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 June 2025.

Thu 7/87:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 10/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 25/6C$ 220
Wed 12/119:00 p.m.YYZ - ORD
Nonstop1h 59mLufthansa
Fri 14/116:20 p.m.ORD - YYZ
1 stop4h 26mLufthansa
Deal found 24/6C$ 223
Sat 9/86:15 a.m.YYZ - ORD
1 stop4h 37mAir Canada
Sat 16/810:40 a.m.ORD - YYZ
1 stop5h 25mAir Canada
Deal found 25/6C$ 231
Fri 22/88:25 a.m.YTZ - ORD
1 stop7h 30mAir Canada
Mon 25/810:40 a.m.ORD - YTZ
1 stop5h 06mAir Canada
Deal found 23/6C$ 232
Fri 12/91:00 p.m.YYZ - ORD
Nonstop2h 01mUnited Airlines
Tue 16/98:55 a.m.ORD - YYZ
Nonstop1h 54mUnited Airlines
Deal found 25/6C$ 234
Sun 12/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Mon 20/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 25/6C$ 237
Sun 2/115:15 p.m.YYZ - ORD
1 stop5h 50mAmerican Airlines
Tue 4/118:05 a.m.ORD - YYZ
1 stop7h 29mAmerican Airlines
Deal found 25/6C$ 253
Wed 6/86:30 a.m.YYZ - ORD
1 stop7h 20mWestJet
Sun 10/86:00 a.m.ORD - YYZ
1 stop4h 59mWestJet
Deal found 23/6C$ 257
Thu 2/106:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Wed 8/109:47 a.m.ORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 26/6C$ 258
Mon 21/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 27/79:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 24/6C$ 258
Wed 20/812:48 p.m.YYZ - MDW
1 stop5h 49mWestJet
Sat 23/810:31 a.m.MDW - YYZ
1 stop5h 26mWestJet
Deal found 25/6C$ 263
Thu 7/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 14/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 25/6C$ 273

Cheapflights Fare Finder

Customize your flight search to find flights from Canada to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 June 2025.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 10/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

9:00 p.m.-9:59 p.m.

Nonstop1h 59m

Chicago O'Hare Intl

Fri 14/11

6:20 p.m.-11:46 p.m.

1 stop4h 26m

C$ 223

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/8

6:15 a.m.-9:52 a.m.

1 stop4h 37m

Chicago O'Hare Intl

Sat 16/8

10:40 a.m.-5:05 p.m.

1 stop5h 25m

C$ 231

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 22/8

8:25 a.m.-2:55 p.m.

1 stop7h 30m

Chicago O'Hare Intl

Mon 25/8

10:40 a.m.-4:46 p.m.

1 stop5h 06m

C$ 232

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/9

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Tue 16/9

8:55 a.m.-11:49 a.m.

Nonstop1h 54m

C$ 234

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 12/10

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Mon 20/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 2/11

5:15 p.m.-10:05 p.m.

1 stop5h 50m

Chicago O'Hare Intl

Tue 4/11

8:05 a.m.-4:34 p.m.

1 stop7h 29m

C$ 253

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 6/8

6:30 a.m.-12:50 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/8

6:00 a.m.-11:59 a.m.

1 stop4h 59m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 27/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 258

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 2/10

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Wed 8/10

9:47 a.m.-12:32 p.m.

Nonstop3h 45m

C$ 258

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/6

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago

What is the cheapest month to book a flight from Canada to Chicago?

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada to Chicago in March is currently the most expensive (average of C$ 351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CA to CHI?

Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 26 June 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.

Weekly flight availability from Canada to Chicago

Explore weekly flight availability from Canada to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 26 June 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 26 June 2025.
Check out reviews from past customers who have flown with Delta,Alaska Airlines, andPorter Airlines from Canada to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Alaska Airlines
8.0
Very good
10,000 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Porter Airlines
8.0
Very good
293 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Hawaiian Airlines
7.8
Good
2,522 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Transat
7.8
Good
401 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Canada to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Canada to Chicago one-way?

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at C$ 149. American Airlines flights start at C$ 152 while deals on Air Canada start at C$ 153 one-way.

  • What are the most popular routes from Canada to Chicago?

    When deciding which route to take from Canada to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Vancouver Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: Copa Airlines (96%), SkyWest Airlines (93%), ANA( 93%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 187. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 198 on average our data indicates C$ 1,353 when flying from Canada to Chicago.

  • Can I find deals for flights from Canada to Chicago that include hotel bookings?

    Yes. In addition to deals on Canada to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Chicago.

  • Can I find deals for business class flights from Canada to Chicago?

    Yes. Cheapflights offers flight deals from Canada to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Canada to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada to Chicago in March is currently the most expensive (average of C$ 351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
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Fort McMurray to O'Hare Intl flights
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Los Angeles to O'Hare Intl flights
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Victoria to Midway flights
Seattle to O'Hare Intl flights
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Buffalo to St. Louis flights
Saskatoon to Midway flights

Top 7 airlines flying from Canada to Chicago

Discover the top 7 airlines that operate flights from Canada to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 26 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 148AverageC$ 484FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 169AverageC$ 479FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 176AverageC$ 484FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 197AverageC$ 483FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Porter AirlinesCheapestC$ 231AverageC$ 414FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 240AverageC$ 539FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapestC$ 355AverageC$ 494FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Canada to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Canada to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Canada to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Canada shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Canada to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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